EP0184122A2 - Sulfamoylharnstoffderivate - Google Patents

Sulfamoylharnstoffderivate Download PDF

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Publication number
EP0184122A2
EP0184122A2 EP85115026A EP85115026A EP0184122A2 EP 0184122 A2 EP0184122 A2 EP 0184122A2 EP 85115026 A EP85115026 A EP 85115026A EP 85115026 A EP85115026 A EP 85115026A EP 0184122 A2 EP0184122 A2 EP 0184122A2
Authority
EP
European Patent Office
Prior art keywords
compound
alkyl
methyl
mixture
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85115026A
Other languages
English (en)
French (fr)
Other versions
EP0184122B1 (de
EP0184122A3 (en
Inventor
Barry Van Gemert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PPG Industries Inc
Original Assignee
PPG Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/677,617 external-priority patent/US4559081A/en
Priority claimed from US06/689,001 external-priority patent/US4566959A/en
Application filed by PPG Industries Inc filed Critical PPG Industries Inc
Publication of EP0184122A2 publication Critical patent/EP0184122A2/de
Publication of EP0184122A3 publication Critical patent/EP0184122A3/en
Application granted granted Critical
Publication of EP0184122B1 publication Critical patent/EP0184122B1/de
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • This invention relates to herbicidally active sulfamoyl urea derivatives, including herbicidal formulations uses thereof to control the growth of noxious plants, i.e., weeds.
  • This invention concerns sulfamoyl urea derivatives represented by the Formula I: wherein: Z is N or CH;
  • the Formula I compounds may conveniently be prepared by reacting a suitably substituted amino pyrimidine or amino triazine of the Formula II: wherein R 1 , R 2 , R 3 and Z are as previously defined, with a halosulfonyl isocyanate of the formula OCN-SO 2 -Hal, wherein Hal is halogen, e.g., chlorine, fluorine or bromine to form the corresponding halosulfonyl urea of the Formula III:
  • Formula III compound is then reacted in the presence of an acid accepting agent with at least a stoichiometric amount of a suitably substituted amine of the Formula IV: wherein R 4 and R are as previously defined, to form a Formula I compound of the invention.
  • Preferred compounds of the invention are those wherein R 3 , R 4 and R 6 are hydrogen and Z is N. Preparation of particularly preferred compounds of the invention are illustrated by the following Examples:
  • Weed control in accordance with this invention is effected by applying to the soil prior to emergence of weeds therefrom or to the plant surfaces subsequent to emergence from the soil, a herbicidally effective amount of a compound of this invention. It is, of course, to be understood that the term "a compound of this invention” also includes mixtures of such compounds or a formulation containing a compound or mixture of compounds of this invention.
  • herbicidally effective amount is amount of a compound of this invention required to so injure or damage weeds such that the weeds are incapable of recovering following application, while not causing any substantial damage to any valuable crop amongst which the weeds might be growing.
  • the quantity of a compound of this invention applied in order to exhibit such satisfactory herbicidal effect may vary over a wide range and depends on a variety of factors, such as, for example, hardiness of a particular weed species, extent of weed infestation, climatic conditions, soil conditions, method of application, and the like.
  • weed control typically, as little as one or less pound per acre of a compound of this invention would be expected to provide satisfactory weed control, although in some instances application rates in excess of one pound per acre; e.g., up to 5 or more pounds per acre might be required.
  • efficacy of a particular compound against a particular weed species may readily be determined by routine laboratory or field testing in a manner well known to the art. It is expected that satisfactory weed control can be had at a rate of application in the range of 0.01 to 2.0 pounds per acre.
  • a compound of this invention can be formulated according to routine methods with any of several known and commonly used herbicidal diluents, adjuvants and carriers.
  • the formulations can contain liquid carriers and adjuvants such as organic solvents, as well as emulsifiers, stabilizers, dispersants, suspending agents, spreaders, penetrants, wetting agents and the like.
  • Typical carriers utilized in dry formulations include clay, talc, diatomaceous earth, silica and the like.
  • Preferred formulations are those in the form of wettable powders, flowables, dispersible granulates or aqueous emulsifiable concentrates which can be diluted with water at the site of application.
  • dry formulations such as granules, dusts, and the like, may be used.
  • a compound of this invention can be applied in combination with other herbicidal agents in an effort to achieve even broader vegetative control.
  • Typical herbicides which can be conveniently combined with Formula I compound include atrazine, hexazinone, metribuzin, ametryn, cyanazine, cyprazine, prometon, prometryn, propazine, simazine, terbutryn, propham, alachlor, acifluorfen, bentazon, metolachlor and N,N-dialkyl thiocarbamates such as EPTC, butylate or vernolate.
  • herbicides may be used in combination with a compound or compounds of the invention.
  • formulations will contain from about 5 to about 95 percent by weight of a compound of this invention.
  • the herbicidal formulations contemplated herein can be applied by any of several method known to the art.
  • the formulation will be surface applied as an aqueous spray.
  • Such application can be carried out by conventional ground equipment, or if desired, the sprays can be aerially applied. Soil incorporation of such surface applied herbicides is accomplished by natural leaching, and is of course facilitated by natural rainfall and melting snow. If desired, however, the herbicides can be incorporated into the soil by conventional tillage means.
  • Compounds of this invention are believed effective for preemergence or postemergence control of a wide variety of broadleaf and grassy weeds.
  • Typical of the various species of vegetative growth that may be controlled, combated, or eliminated are, for example, annuals such as pigweed, lambsquarters, foxtail, crabgrass, wild mustard, field pennycress, ryegrass, goose grass, chickweed, wild oats, velvetleaf, purslane, barnyardgrass, smartweed, knotweed, cocklebur, kochia, medic, ragweed, hemp nettle, spurrey, pondweed, carpetweed, morningglory, ducksalad, cheatgrass, fall panicum, jimsonweed, witchgrass, watergrass, wild turnip, and similar annual grasses and weeds.
  • Biennials that may be controlled include wild barley, campion, burdock, bull thistle, roundleaved mallow, purple star thistle, and the like. Also controlled by the compounds of this invention are perennials such as quackgrass, Johnsongrass, Canada thistle, curly dock, field chickweed, dandelion, Russian knapweed aster, horsetail, ironweed, sesbania, cattail, wintercress, horsenettle, nutsedge, milkweed, sicklepod, and the like.
  • the compounds prepared in the Examples were each tested for preemergence and postemergence herbicidal activity by spraying a solvent solution of same on a variety of common broadleaf and grassy weed species, under controlled laboratory conditions of light, temperature and humidity.
  • the extent of herbicidal injury was evaluated, periodically after application, and a Numerical Injury Rating (NIR) assigned on a scale of from 0 (no injury) to 10 (all plants dead).
  • NIR Numerical Injury Rating

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP19850115026 1984-12-03 1985-11-27 Sulfamoylharnstoffderivate Expired EP0184122B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/677,617 US4559081A (en) 1984-12-03 1984-12-03 Sulfamoyl urea derivatives
US677617 1984-12-03
US06/689,001 US4566959A (en) 1984-01-05 1985-01-04 Process for the electrochemical roughening of aluminum useful for printing plate supports, in an aqueous mixed electrolyte
US689001 1985-02-04

Publications (3)

Publication Number Publication Date
EP0184122A2 true EP0184122A2 (de) 1986-06-11
EP0184122A3 EP0184122A3 (en) 1987-09-02
EP0184122B1 EP0184122B1 (de) 1991-07-17

Family

ID=27101841

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19850115026 Expired EP0184122B1 (de) 1984-12-03 1985-11-27 Sulfamoylharnstoffderivate

Country Status (1)

Country Link
EP (1) EP0184122B1 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0463287A1 (de) * 1990-06-22 1992-01-02 American Cyanamid Company 1-((0-Cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidyl)harnstoff und Verfahren zu seiner Herstellung
WO1996010566A1 (de) * 1994-10-04 1996-04-11 Bayer Aktiengesellschaft Substituierte phenylaminosulfonylharnstoffe als herbizide
EP0849262A1 (de) * 1996-12-20 1998-06-24 American Cyanamid Company Aminophenyl-Keton-Derivate und eine Methode für ihre Herstellung
US6127576A (en) * 1996-12-20 2000-10-03 American Cyanamid Company Aminophenyl ketone derivatives and a method for the preparation thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2110689A (en) * 1981-12-03 1983-06-22 Sandoz Ltd Herbicidal heterocyclic aminosulfonyl ureas and isoureas
CH649081A5 (de) * 1982-01-12 1985-04-30 Ciba Geigy Ag Triaza-verbindungen.

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0463287A1 (de) * 1990-06-22 1992-01-02 American Cyanamid Company 1-((0-Cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidyl)harnstoff und Verfahren zu seiner Herstellung
TR25504A (tr) * 1990-06-22 1993-05-01 American Cyanamid Co 1-(0-(siklopropilkarbonil) fenil) sulfamoil-) 3-(4,6-dimetoksit-2-pirimidinil) urea ve bunun hazirlanmasi icin usul.
CN1069813C (zh) * 1990-06-22 2001-08-22 美国氰胺公司 1－{[邻－(环丙基羰基)－苯基]－氨磺酰}－3－(4,6－二甲氧基－2－嘧啶基)脲除草剂
WO1996010566A1 (de) * 1994-10-04 1996-04-11 Bayer Aktiengesellschaft Substituierte phenylaminosulfonylharnstoffe als herbizide
EP0849262A1 (de) * 1996-12-20 1998-06-24 American Cyanamid Company Aminophenyl-Keton-Derivate und eine Methode für ihre Herstellung
US6127576A (en) * 1996-12-20 2000-10-03 American Cyanamid Company Aminophenyl ketone derivatives and a method for the preparation thereof
CN1100755C (zh) * 1996-12-20 2003-02-05 美国氰胺公司 氨基苯基酮衍生物及其制备方法

Also Published As

Publication number Publication date
EP0184122B1 (de) 1991-07-17
EP0184122A3 (en) 1987-09-02

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